Real Estate Investment Properties for Sale in Chester, MD

Looking for investment property in Chester, MD with high ROI ?

Explore a variety of short-term homes & houses in Chester, MD. Invest wisely with VRBO & Chester, MD Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Condos for Sale in Chester, MD

Search for Condo for Sale in Chester, Maryland. Browse all of Mashvisor’s Condo listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 23 Condo listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1012 AUCKLAND Way CHESTER, MD Experience the best of Kent Island waterfront living in this beautifully appointed home lo...	3 beds \| 4 baths \| 2,076 sq.ft.	$599,900	Airbnb cash on cash: 0.51% Traditional cash on cash: 4.17% Airbnb Rental Income: $2714 Traditional Rental Income: $4122 Airbnb ROI: 0.51% Traditional ROI: 4.17%
34-E QUEEN ANNE Way CHESTER, MD WATERFRONT Condo! Open House to be scheduled soon! Beautifully renovated 2BR/2.5BA waterfr...	2 beds \| 3 baths \| 1,586 sq.ft.	$515,000	Airbnb cash on cash: 0.24% Traditional cash on cash: 3.53% Airbnb Rental Income: $2009 Traditional Rental Income: $3067 Airbnb ROI: 0.24% Traditional ROI: 3.53%
2008 BRIDGEPOINTE Drive CHESTER, MD Welcome to this gorgeous end unit townhouse offering low-maintenance living in a highly co...	2 beds \| 2 baths \| 1,804 sq.ft.	$380,000	Airbnb cash on cash: 1.5% Traditional cash on cash: 4.97% Airbnb Rental Income: $2009 Traditional Rental Income: $2725 Airbnb ROI: 1.5% Traditional ROI: 4.97%
5011 BRIDGEPOINTE Drive CHESTER, MD Nestled in the heart of Kent Island, this charming 3 Bedroom, 2 Full Bathroom townhome wit...	3 beds \| 3 baths \| 1,302 sq.ft.	$374,900	Airbnb cash on cash: 3.3% Traditional cash on cash: 4.63% Airbnb Rental Income: $2714 Traditional Rental Income: $2543 Airbnb ROI: 3.3% Traditional ROI: 4.63%
1025 DUNDEE Court CHESTER, MD Estate Sale! Motivated Seller offering $5,000.00 in closing costs help! OPEN House this Sa...	3 beds \| 3 baths \| 1,400 sq.ft.	$324,900	Airbnb cash on cash: 4.02% Traditional cash on cash: 5.77% Airbnb Rental Income: $2714 Traditional Rental Income: $2606 Airbnb ROI: 4.02% Traditional ROI: 5.77%
4000 HERONS NEST Way #22 CHESTER, MD Four Seasons @ Kent Island - 55+ Community - Price Improvement + Seller to Credit $4000 to...	2 beds \| 3 baths \| 1,900 sq.ft.	$530,000	Airbnb cash on cash: -1.32% Traditional cash on cash: 2.37% Airbnb Rental Income: $2009 Traditional Rental Income: $3311 Airbnb ROI: -1.32% Traditional ROI: 2.37%
106 BODYS NECK Road CHESTER, MD Welcome to Bayside, where coastal living and resort-style amenities come together in one o...	3 beds \| 3 baths \| 1,595 sq.ft.	$435,000	Airbnb cash on cash: 1.47% Traditional cash on cash: 3.33% Airbnb Rental Income: $2714 Traditional Rental Income: $2829 Airbnb ROI: 1.47% Traditional ROI: 3.33%
190 HARRIER Way #24 CHESTER, MD Built for low-maintenance living, this beautiful 3-bedroom, 2.5-bath condo offers 2,600 sq...	3 beds \| 3 baths \| 2,602 sq.ft.	$650,000	Airbnb cash on cash: 0.14% Traditional cash on cash: 1.47% Airbnb Rental Income: $2714 Traditional Rental Income: $2881 Airbnb ROI: 0.14% Traditional ROI: 1.47%
54-H QUEEN CAROLINE CT CHESTER, MD DON""T MISS OUT on this super deal!! Owners have lowered the price by $10,000 and are will...	2 beds \| 3 baths \| N/A	$329,000	Airbnb cash on cash: 0.89% Traditional cash on cash: 2.76% Airbnb Rental Income: $2009 Traditional Rental Income: $2064 Airbnb ROI: 0.89% Traditional ROI: 2.76%
3-D QUEEN VICTORIA Court CHESTER, MD Welcome home to Queens Landing. One bedroom condo with open concept kitchen and living roo...	1 beds \| 1 baths \| 724 sq.ft.	$269,000	Airbnb cash on cash: 0.93% Traditional cash on cash: 3.02% Airbnb Rental Income: $1403 Traditional Rental Income: $1511 Airbnb ROI: 0.93% Traditional ROI: 3.02%
8-F QUEEN VICTORIA WAY CHESTER, MD Queens Landing - One bedroom condo with living room overlooking kitchen, good for entertai...	1 beds \| 1 baths \| N/A	$240,000	Airbnb cash on cash: 1.16% Traditional cash on cash: 2.61% Airbnb Rental Income: $1403 Traditional Rental Income: $1309 Airbnb ROI: 1.16% Traditional ROI: 2.61%
2000 HERONS NEST Way #401 CHESTER, MD Newly adjusted price. Please visit me at the OPEN HOUSE this Sunday from 1-3pm. Rarely ava...	3 beds \| 3 baths \| 2,602 sq.ft.	$700,000	Airbnb cash on cash: -0.51% Traditional cash on cash: 1.42% Airbnb Rental Income: $2714 Traditional Rental Income: $3328 Airbnb ROI: -0.51% Traditional ROI: 1.42%
111 MARSHGRASS WAY #43 CHESTER, MD Penthouse Unit! Seller offering closing cost assistance to qualified buyers! Rare top floo...	2 beds \| 3 baths \| N/A	$765,000	Airbnb cash on cash: -0.99% Traditional cash on cash: 1.26% Airbnb Rental Income: $2009 Traditional Rental Income: $3087 Airbnb ROI: -0.99% Traditional ROI: 1.26%
1000 HERONS NEST Way #22 CHESTER, MD BACK on the MARKET. GREAT OPPORTUNITY at THIS PRICE. This Chester model has scenic, season...	2 beds \| 3 baths \| 1,900 sq.ft.	$485,000	Airbnb cash on cash: -1.19% Traditional cash on cash: 2.6% Airbnb Rental Income: $2009 Traditional Rental Income: $3207 Airbnb ROI: -1.19% Traditional ROI: 2.6%
132 WHEELHOUSE WAY #11 CHESTER, MD Adjusted price and ready for new owners!! Experience everything Four Seasons has to offer ...	2 beds \| 3 baths \| 2,003 sq.ft.	$729,999	Airbnb cash on cash: -0.69% Traditional cash on cash: 1.93% Airbnb Rental Income: $2009 Traditional Rental Income: $3272 Airbnb ROI: -0.69% Traditional ROI: 1.93%
208 BLENNY Lane CHESTER, MD PRICE REDUCTION! Just like NEW! Welcome Home to this beautifully upgraded 4BR END UNIT Tow...	3 beds \| 4 baths \| 1,899 sq.ft.	$434,900	Airbnb cash on cash: 1.53% Traditional cash on cash: 4.6% Airbnb Rental Income: $2714 Traditional Rental Income: $3322 Airbnb ROI: 1.53% Traditional ROI: 4.6%
111 MARSHGRASS Way #21 CHESTER, MD A rare blend of coastal proximity and refined living unfolds within this beautifully appoi...	3 beds \| 3 baths \| 2,602 sq.ft.	$680,000	Airbnb cash on cash: 0.08% Traditional cash on cash: 1.94% Airbnb Rental Income: $2714 Traditional Rental Income: $3249 Airbnb ROI: 0.08% Traditional ROI: 1.94%
54F QUEEN CAROLINE CT CHESTER, MD Completely remodeled in 2026 with a new kitchen to include new appliances, quartz counters...	3 beds \| 3 baths \| N/A	$359,900	Airbnb cash on cash: 2.4% Traditional cash on cash: 2.2% Airbnb Rental Income: $2714 Traditional Rental Income: $2006 Airbnb ROI: 2.4% Traditional ROI: 2.2%
45-G QUEEN NEVA Court CHESTER, MD Seller is offering closing cost assistance for qualified buyers! This charming townhouse i...	2 beds \| 3 baths \| 1,312 sq.ft.	$349,500	Airbnb cash on cash: 0.9% Traditional cash on cash: 3.47% Airbnb Rental Income: $2009 Traditional Rental Income: $2329 Airbnb ROI: 0.9% Traditional ROI: 3.47%
129 WHEELHOUSE WAY #11 CHESTER, MD Buyers got cold feet- Back on Market but won't last long! Priced well below market value! ...	2 beds \| 3 baths \| N/A	$585,000	Airbnb cash on cash: -0.73% Traditional cash on cash: 1.73% Airbnb Rental Income: $2009 Traditional Rental Income: $2827 Airbnb ROI: -0.73% Traditional ROI: 1.73%
1000 HERONS NEST Way #43 CHESTER, MD Beautiful fourth-floor condo offering nearly 2,000 square feet of living space, featuring ...	2 beds \| 3 baths \| 1,832 sq.ft.	$600,000	Airbnb cash on cash: -0.6% Traditional cash on cash: 2.49% Airbnb Rental Income: $2009 Traditional Rental Income: $3218 Airbnb ROI: -0.6% Traditional ROI: 2.49%

Your search for investment property begins and ends here

Condos for Sale in Chester, MD

1012 AUCKLAND Way

CHESTER, MD

3 beds | 4 baths | 2,076 sq.ft.

$599,900

Airbnb cash on cash: 0.51%

Traditional cash on cash: 4.17%

Airbnb Rental Income: $2714

Traditional Rental Income: $4122

Airbnb ROI: 0.51%

Traditional ROI: 4.17%

34-E QUEEN ANNE Way

CHESTER, MD

2 beds | 3 baths | 1,586 sq.ft.

$515,000

Airbnb cash on cash: 0.24%

Traditional cash on cash: 3.53%

Airbnb Rental Income: $2009

Traditional Rental Income: $3067

Airbnb ROI: 0.24%

Traditional ROI: 3.53%

2008 BRIDGEPOINTE Drive

CHESTER, MD

2 beds | 2 baths | 1,804 sq.ft.

$380,000

Airbnb cash on cash: 1.5%

Traditional cash on cash: 4.97%

Airbnb Rental Income: $2009

Traditional Rental Income: $2725

Airbnb ROI: 1.5%

Traditional ROI: 4.97%

5011 BRIDGEPOINTE Drive

CHESTER, MD

3 beds | 3 baths | 1,302 sq.ft.

$374,900

Airbnb cash on cash: 3.3%

Traditional cash on cash: 4.63%

Airbnb Rental Income: $2714

Traditional Rental Income: $2543

Airbnb ROI: 3.3%

Traditional ROI: 4.63%

1025 DUNDEE Court

CHESTER, MD

3 beds | 3 baths | 1,400 sq.ft.

$324,900

Airbnb cash on cash: 4.02%

Traditional cash on cash: 5.77%

Airbnb Rental Income: $2714

Traditional Rental Income: $2606

Airbnb ROI: 4.02%

Traditional ROI: 5.77%

4000 HERONS NEST Way #22

CHESTER, MD

2 beds | 3 baths | 1,900 sq.ft.

$530,000

Airbnb cash on cash: -1.32%

Traditional cash on cash: 2.37%

Airbnb Rental Income: $2009

Traditional Rental Income: $3311

Airbnb ROI: -1.32%

Traditional ROI: 2.37%

106 BODYS NECK Road

CHESTER, MD

3 beds | 3 baths | 1,595 sq.ft.

$435,000

Airbnb cash on cash: 1.47%

Traditional cash on cash: 3.33%

Airbnb Rental Income: $2714

Traditional Rental Income: $2829

Airbnb ROI: 1.47%

Traditional ROI: 3.33%

190 HARRIER Way #24

CHESTER, MD

3 beds | 3 baths | 2,602 sq.ft.

$650,000

Airbnb cash on cash: 0.14%

Traditional cash on cash: 1.47%

Airbnb Rental Income: $2714

Traditional Rental Income: $2881

Airbnb ROI: 0.14%